🎃 EXCLUSIVE HALLOWEEN SALE—ONLY 15% DEPOSIT FOR ALL 2025 TRIPS 🎃

Sailboat Charter in Caribbean - Yacht Hire

Sailboats for rent in Caribbean

202 boats available

Hero image

Filters

Trustpilot

Exclusive Deals

Take your boat holidays to the next level with exclusive boat deals featuring free and exciting add-ons!

See exclusive dealsbackground

Can't find what you want?Talk to our holiday planners today.

Frequently asked questions

What happens when I request a quote?

Once we receive your request, we will confirm the availability of the boat, as well as check for alternative ones. To ensure your experience is the best it can be, we may contact you to discuss your request in detail. Let us do the research for you - free of charge.

When can I get in touch with the captain/skipper?

The timing depends on your charter type. For crewed charters, we can provide the captain's contact details upon request. For bareboat charters with a hired skipper, you can request the contact information 1-3 weeks before departure.

What is the Charter Fee?

The Charter Fee is an additional, obligatory cost, which typically includes the end cleaning of the boat, home port fees, and linen & towels. The details of the charter fee differ depending on the boat, location and charter partner.

Are there any other costs I should be aware of?

There are marina fees and fuel costs which vary depending on the type, duration and location of your sailing holiday. Marina fees need to be paid at each marina you choose to dock overnight - the amount varies but you may be able to find this information in advance by contacting the marinas directly. Fuel costs depend on whether you’re sailing a motorboat or a sailboat. You can estimate fuel costs by double-checking your chosen boat’s engine, and the expected distance you aim to sail.

Sailing on a sailboat in the Caribbean

Charter a sailboat in the Caribbean for the most exciting adventure. Admire secluded islands full of white sandy beaches, palm trees and surrounded by clear turquoise waters. A sailboat gives you the freedom to explore the islands you want to see at your own pace.

The pros of renting a sailboat in the Caribbean

Renting a sailboat in the Caribbean provides you with the freedom to explore the stunning Caribbean islands at your own pace. You decide where you go, sail along secluded islands and beaches, as well as discover hidden gems that are often inaccessible by other means of transportation. After all, there are no airplanes heading to the most secluded beaches.

A sailing yacht charter in the Caribbean allows you to explore this beautiful place on earth more sustainably. Sailboats solely run on wind, making them one of the most sustainable options when it comes to boat holidays in the Caribbean. They don’t produce additional CO2-emissions and don’t disturb the environment with noise pollution.

Sailing in the Caribbean comes with even more advantages than you might think. You can sail quite autonomously, because you don’t need to return to the marinas frequently in order to refuel your tank. In fact, you can go a whole week or more without going back to a marina - if you stocked up on enough food that is.

The cons of renting a sailboat in the Caribbean

While there are very many advantages to sailing in the Caribbean, there are also some things to keep in mind when doing so. Sailboats solely run on wind, which certainly makes them more sustainable, but also highly dependent on mother nature. You might get stuck in the middle of the sea or you might not even be able to leave the port when the winds are too strong and the ocean too dangerous.

Another thing to keep in mind when chartering a sailboat in the Caribbean is the fact that the cabins probably won’t be the most comfortable and biggest you have ever slept in. They certainly can’t keep up with the level of comfort you get when sleeping on board a catamaran, but comfort probably isn’t the main reason you would book a sailboat in the Caribbean, is it?

How many people can go on a sailboat in the Caribbean?

Most sailboats in the Caribbean offer enough space for 7 to 13 people to sleep on board the boat, but the majority of sailboats you can charter here offer space for eight people. This allows for an intimate sailing experience with your closest friends or family. The bedrooms might be small, but you probably won’t spend much time under deck anyway.

When is the best time to sail on a sailboat in the Caribbean?

The best time to sail in the Caribbean on a sailboat is between December and May. It’s dry, you get plenty of sunshine and the winds are reliable, but not too strong. During these months the winds are strongest in December and January, due to the Easterly Trade Winds, making for ideal sailing conditions. In general you can expect wind strengths of around 10-25 knots. You should definitely avoid sailing in late summer during hurricane season, as this could potentially catapult you into a life threatening situation.

Sailboat rental prices in Caribbean

A boat holiday in the Caribbean is certainly not something you would do when travelling on a budget, but a sailboat charter in the Caribbean is definitely one of the more affordable options when it comes to vacationing here. You can expect to pay between 3.500 EUR and 30.000 EUR per week. It’s all up to your budget. If you don’t want to sail the sailboat yourself, you can always hire a skipper in addition to your sailboat charter in the Caribbean. This will cost you extra, but you can lean back and simply enjoy your sailing vacation in the Caribbean.

What kind of boat licence do I need when renting a sailboat in the Caribbean?

Good news: Anyone who wants to sail in the Caribbean can do so without a boat licence. The charter will certainly give you instructions upon arrival on how to operate the sailboat and other useful information, but then it’s up to you. However, as sailboats are much harder to operate than motorboats, you will need some prior sailing experience in order to safely maneuver them across the water.

The best routes for sailboats in the Caribbean

The Caribbean offers numerous breathtaking routes for sailboats, each with its own highlights and attractions. Here are some of the best routes to consider when sailing on a sailboat in the Caribbean:

 

The Virgin Islands Route: This route explores the British Virgin Islands and the U.S. Virgin Islands. It is renowned for its pristine beaches, crystal-clear waters, and vibrant marine life. You can visit popular destinations such as Tortola, Jost Van Dyke, Virgin Gorda, and St. Thomas, while also discovering hidden coves and secluded anchorages. There are also quite a few beaches that you can only reach by boat. White Bay on Jost van Dyke will be a dream come true and you can safely anchor with plenty of other boats around. Loblolly Bay on Anegada is a white sandy beach surrounded by the clearest turquoise waters you can imagine. You will truly feel like you have arrived in paradise!

 

The Grenadines Route: This route takes you through the picturesque Grenadine Islands, including St. Vincent, Bequia, Mustique, Tobago Cays, and Grenada. The Grenadines offer stunning coral reefs, white sandy beaches, and a laid-back island atmosphere. It's a paradise for snorkeling, diving, and exploring charming fishing villages. The main island, St Vincent, offers plenty of amazing opportunities to go diving. Wallilabou Bay is one of the most popular spots here.


The Bahamas Route: While technically not part of the Caribbean Sea, the Bahamas are still considered a popular sailing destination in the Caribbean. This route takes you through the stunning Exumas, Abacos, and to its beautiful capital Nassau. The Bahamas offer pristine turquoise waters, countless secluded cays, and some of the best diving and snorkeling spots in the world. If you don’t just want to spend your days sunbathing and admiring the nature of the Bahamas, you should definitely explore Nassau’s vibrant nightlife.

Discover Borrow A Boat